Awakening to my Fem Self

Story Info
Str8 guy feminized by couple with a car accident's assist.
3.1k words
4.61
23.2k
42
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
moonsissy
moonsissy
251 Followers

*Much of this story is true, though some specifics were changed and a couple events combined.*

Even though his hands were on my head, I was able to tilt back enough to see his eyes looking down at me. There I was with his thick cock filling my mouth, saliva and pre-cum running down my chin, and my heart pounding from the thrill of it all.

"Come on! Be a good girl, don't keep me on edge," he moaned, "I'm about to give you what you crave. Suck that dick you cum hungry bitch."

And with that I began bobbing up and down, even faster than before. Knowing that he would soon fill my mouth with his seed was enough motivation to suck like a hungry vampire.

"That's it baby, suck my dick you little slut. Oh yeah... No one sucks dick better than a pretty sissy fag, oh fuck...yeah, fuck yeah..." And just like that my mouth and throat were being filled with his warm sperm.

His cock was softening in my mouth as the last of his seed spilled out. He pulled back from me and put his dick back in his pants and walked away. I knelt there in the club parking lot, savoring the taste in my mouth. I so love making men cum.

Less than four years before I would never have imagined that I, Kevin Paris, would be on my knees, swallowing another man's sperm in a public parking lot while dressed in black fishnet stockings, a garter belt, black bra, red lipstick, and "fuck me" pumps.

I thought of myself as masculine back then. I played tennis and stayed in shape. My body, though not muscular,was lean and toned. I dated women and had sex pretty regularly. I had shoulder length hair and was told I was good looking and even pretty.

Then one day I was in an accident. I needed to get surgery on my neck. For over 6 months after that I was unable to lift anything. Over that time my upper body gradually got thin. My measurements were literally 34"- 28" - 34". I weighed only 135 pounds even though I stood at 5'10". When I looked in the mirror I felt like a boyish flat chested woman was looking back. It was an odd sensation.

To make me feel worse I was at the beach around that time hanging out with some women friends who all joked about how they wished they had a figure as nice as mine. A few times in stores the sales people had called me miss or ma'am. I wasn't getting any dates at that point, either. One woman even told me to my face that she couldn't date a guy who was prettier than she was.

I was having no luck with women, but my sex drive was still strong as ever. I posted a profile on a dating site and wasn't getting any replies. After a few months I had given up and was about to remove my profile from the site when I received a message from a woman saying her and her husband liked my pictures and profiles. They were looking for a slender guy to join them for some fun. At first I didn't know what to think about joining a couple. Then she sent some pictures of herself partially naked and in sexy lingerie. There was no way I could say no. She was blond, with beautiful firm looking breasts and long legs. So I wrote back, saying I would love to meet.

She said her name was Marci and her husband was Michael. They were glad to hear I was interested. Then she wrote that there were certain things I needed to do if I was serious about getting together. I needed to shave all the hair from my body, though I could leave a little runway strip. I needed to wear a thong or g-sting when I met them and to show I was serious I had to take a picture to prove I did it. If she liked it, I could come over that night. Marci also wrote, " I get so turned on by guys who can be comfortable with their feminine side. I don't need another alpha male in my bed. Michael is more than enough."

I was taken aback. She wanted to feminize me. It was bad the way it was with my girlish body but now the only way I was going to get laid was if I was even more girlish? I was about to write back that I didn't think I could do it when a picture popped up of her, touching her naked breast and her legs spread and I got instantly excited. I then wrote back saying I'd have a picture for her that afternoon.

It was embarrassing standing there in the store trying to pick out panties to buy, but for some reason I was buzzing with excitement at the same time. I wasn't sure what size to get. As I looked over some of the thongs a voice startled me.

"Do you need any help miss," It was a sales woman.

Pretending I didn't hear her call me miss I said, "I'm looking to get some underwear for my girlfriend, and not sure what size."

" Oh I'm sorry, I uhh," she stammered. when she caught her composure and said, "well is she slender like you or more full figured?"

"She's shorter than me but I'd say she is lean like me."

"I'd recommend, small or petite size. If it isn't the right fit she can always return them."

I thanked her, picked out three pairs and paid at the self service checkout.

When I got home I removed the hair from my arms, legs and body, not that I really had much anyway, and I left a little runway strip as Marci suggested. I couldn't believe how it looked. It was so sexy. I then slipped on a black thong. It felt so arousing. And when I looked in the mirror I was a bit shocked. It was a woman's body, albeit flat chested. I also realized that body was making me aroused and I was getting hard in the panties I had on. I took a picture with my erection. When I looked at the photo you couldn't even tell I was hard. I knew I didn't have a big package to offer but this was embarrassing. My small dick didn't even stick out of the top of the thong. I lost my erection looking at the pics and took a few more without my hard-on. The shots looked the same. I chose one and sent it to Marci.

Marci replied quickly saying, "Perfect. What a pretty body! We are going to have fun tonight! And by the way, I sometimes like to use my strap-on, so please prepare yourself. See you tonight at 8:00." She sent her address and another enticing nude photo.

"Strap-on"! I was not expecting this. I'd never done anything like that before. I was expecting to fuck her, not the other way around. I was getting second thoughts but every time I looked at her pictures I kept thinking how great it would be to touch her beautiful breasts, to feel myself enter her and to taste her lips. Besides I could always say no thanks to being fucked once I was there. But I did prepare anyway and I showed up at 8:00 on the nose.

"Oh Kerry, you look even prettier in person," Marci said when she opened the door and looked me up and down. She leaned in and kissed me.

I was so pleasantly surprised. She looked hotter than her pics. She was dressed in fishnet stockings, spiked heels, a black corset that pushed her breasts up perfectly, and soft red lipstick.

"Michael will be back shortly. Would you like some wine?" she asked and handed my a glass before I could answer.

"Oh hon, you must strip for me. I want to see you in your little panties. The picture you sent got me so wet. Michael could never wear anything like that. His big cock just overflows. It's comical. But you, well you look like you were made to wear panties. "

It was weird to have a woman emasculate me like that. I felt embarrass yet strangely turned on. I put down my glass and did as she asked. I took off my shirt and dropped my pants to the floor. I was erect in my thong. I tried covering it with my hands.

"Are you being shy, hon? No need to be. You look so cute in your panties. Take your hands away so I can get a better look."

I let my hands drop.

"Oh Kerry, you are a dream. Let's go into the bedroom. I want to put some makeup on you. I'm so wet right now," she took my hand and placed it on the front of her panties, "See! I'm dripping."

She took me to her room, had me sit on the bed and she brought out a makeup bag and started to go to work on me, "You are looking so hot! Michael is going to love you."

All of a sudden I realized Michael was a part of the picture. Here I was as unmanly as you can get, in a thong and wearing makeup and her husband would be here shortly. Many emotions rushed through me, as she continued her makeover of me.

Her last touch was to apply lipstick and then she said, "Oh, I almost forgot one more thing."

She went to the dresser and came back over with a black lacy bra. She had it on me in a flash. She fluffed up my hair and used hairspray. Then she told me to turn around and look in the mirror. I was stunned to see this beautiful woman looking back!

"Oh my god," I barely could get out the words, "That's me? You are magical the way you transformed me... I can't believe it."

"You are fabulous baby. As sexy as any woman I've slept with, " she said as she stepped closer to me. Her hands were touching me all over, we began to kiss.

"Well, don't you girls look hot together," I was startled by a deep male voice. I almost froze. I turned my head to see this shirtless, muscular, tall, black man standing in the doorway. His presence seemed to change the world around us. He was dynamic and powerful and all he was doing was standing there. I never wanted to touch or kiss a man before, but at that moment all I could think about was his sexual energy, his muscular chest and his handsome face.

"Oh Michael," Marci practically screamed as she ran to her husband, "Look at Kerry! Isn't she beautiful? You are going to have so much fun with her."

Here I was just a minute ago standing there in lingerie and makeup, my dick hard as a rock, yet almost invisible in my thong, thinking I was manly enough to have sex with Marci. And just like that, it all changed.

"We knew from your pictures that you were more than just an average white sissy," Michael said directly to me as he removed his pants, revealing a big thick dick. Though it wasn't hard yet, it was already inches longer and thicker than mine. It was dark chocolate in color and brought something out in me that was so primal. I couldn't help but stare as my heart pounded and I thought I would cum just at the site of it, "You are a beauty. I can't wait to fuck you in front of Marci. But first Marci, why don't you show Terry how a good girl appreciates her man?"

In a flash Marci was on her knees kissing and licking that big dick. I was watching her with envy and desire. But, what the hell was going on in my head? I had come here to fuck her. I even went to the extreme by shaving my body and wearing a thong and then letting her put makeup on me, just so I'd be able to fuck her. But here I was watching her worship her husbands BBC and all I wanted to do was get on my knees and do the same. I wanted to feel it, taste it, have it deep in my mouth, my throat.

"Why don't you join her, Terry," Michael woke me from my trance, "It looks like your little clit is swollen up in your panties from desire. We all know you want it don't you girl?"

I couldn't speak. I just nodded and got down on my knees next to his wife. She pulled his dick from her mouth and offered it to my lips. I opened my mouth gladly and at that moment I became a cocksucker.

There was no denying that there was only one real man in the room. A man with a big alpha male cock and the confidence to use it. I was truly aware of my sissy status, with my makeup on, my panties and bra and my little white girl dick.

Marci whispered, "Isn't it fabulous! It's so fucking big. It needs to be shared. And we are the lucky bitches who get to worship this powerful man's big black dick."

All of a sudden I felt her hand slide into my panties, "See how hard your little clit is hon? It feels like it's going to orgasm any second." And it did.

She just rubbed it once up and down like she'd rub a clit and the excitement of having Michael's dick in my mouth brought me over the edge. I grabbed his solid ass cheeks and shuddered as my panties filled up with my orgasm and my cream ran over Marci's fingers. Michael held my head steady and continued to fuck my face. Marci reach up with her cum covered hand and stroked his big dick. I could taste my own cum as I took that cock as deep as I could. It was wonderful. Even though I had just cum I didn't lose the desire to keep sucking. It was instinctual. I wanted his seed in me.

"Oh yes, girl, you are a natural born cocksucker, aren't you?" Michael said as he pulled back from me, "Now let's see how good you can ride my dick."

"Oh, hon, let me do her first. Let me get little miss Terry ready for your big cock," Marci pleaded. She had already gotten out her strap-on and was getting it ready with lube.

Michael sat back on the bed and told me to bend over and continue to suck his cock, "Slip off your panties and spread your legs sissy girl, you are about to be fucked while sucking dick."

I did as told. I spread my legs with my ass in the air, bent down and took his cock-head in my mouth. Marci slid a lubed finger slowly into me. My little dick was no longer nestled in my wet panties, it just hung there like a tiny pinky. It was a strange sensation but I liked it. I started to focus on Michaels black meat in my mouth. At some point I realized something bigger than Marci's finger was slowly and painfully thrusting into me. The more she moved back and forth the deeper it got then she stopped and I tried to relax. It was feeling better and better. Then she started thrusting again, hard.

"Oh fuck, yeah," she screamed out, "fuck this feels so good.... Oh, yes..." She grabbed my hips and fucked me hard. I loved it. A big cock in my throat and a woman fucking me with a strap-on was pleasure beyond belief.

Marci was obviously having an intense orgasm. I was having sensations pulsing though me that I'd never experienced before. And that cock in my mouth made everything even hotter.

Marci was spent and leaned her body on top of me as the dildo slipped out. "Oh my god that was such an intense orgasm, she moaned and then said to Michael, "She's a bit tight hon, be gentle with her."

Michael pulled my head up from his cock, "spit on it pretty girl. I'm going to show you how a real man fucks a white sissy bitch. Tell me you want it."

I didn't hesitate, "Oh, Michael, I want it more than I have ever wanted anything else. I am not ashamed to admit it either. I want your big black cock in my sissy pussy. I want you to fill me with your seed."

"Just stay like that, with this sweet little ass of yours in the air waiting."

He got behind me, I felt his cock-head attempting to enter me.

"Relax and it won't hurt as much. I'll take it slow, but once I am in, I am going to fuck the hell of you."

Just like he said he would, he took it slow. At one point he had to push hard and it hurt, but once he was in it felt amazing. He then started slapping my ass and thrusting hard. As he fucked me he said, "Yes, Kerry you are my bitch now. I'm going to breed your white tranny ass."

As he thrust into me harder and harder and continued talking nasty, I began to have an orgasm. It was incredible! I actually felt like I was crossing over to another world or dimension. I don't know how long it lasted but it seemed to go on and on. I was screaming in a light whimper. I had never had an orgasm like this before. I felt Michaels hand slap my ass. It felt so right. Crystal clear cum or was it pre-cum flowed out of my tiny dick.

"Fuck this is one fucking sweet ass," he called out, "Yes, bitch, you want my cum, here it is... Oh yes, fuck, damn."

He was a wild beast, thrusting and grabbing my hips then pulling my hair, talking nasty and I felt him cum inside me. Still he kept ramming into me and I started to cum again. My god, I was a fem bitch, a powerful black man's sissy. I was loving it. I came here to fuck a woman's pussy, only to find I wanted cock to fuck me even more. From then on I knew my place in the sexual world. I was a cock worshipper, a cocksucker, a fem sissy, a fuck toy and proud of it.

moonsissy
moonsissy
251 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
AnonymousAnonymous7 months ago

I can't stand it when people call a dick a clit, just sounds stupid.

MatureandkinkyMatureandkinkyabout 1 year ago

The Stuff of My Dreams !!!

Your story took me to a place I crave. I’m probably passed my “use by” date and I will never get to savour such a reality, but your story and my imagination has me so horny and needy!

5 Star wish it could be many more. Thank you 👏😜😉

AnonymousAnonymousabout 1 year ago

The true story bit just makes us laugh at you and does nothing for the story. The minute he sticks his cock in your mouth you bite it off and the story is done. Just awful

AnonymousAnonymousover 1 year ago

I love to read about feminization transformations of young attractive men. They really do appreciate the help and support to completely give in to the lifestyle they crave.

petey377petey377over 1 year ago

lucky sissy understands his place in the world

Show More
Share this Story

Similar Stories

A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Pretty boy to Sissy girl Married pretty boy enjoys being cuckolded.in Transgender & Crossdressers
More Stories